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[ CAS No. 66521-66-2 ] {[proInfo.proName]}

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Chemical Structure| 66521-66-2
Chemical Structure| 66521-66-2
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Product Details of [ 66521-66-2 ]

CAS No. :66521-66-2 MDL No. :MFCD01317832
Formula : C9H8N4 Boiling Point : -
Linear Structure Formula :- InChI Key :LQHQKYWYKPLKCH-UHFFFAOYSA-N
M.W : 172.19 Pubchem ID :12450582
Synonyms :
4-(3-Pyridinyl)-2-aminopyrimidine
Chemical Name :4-(Pyridin-3-yl)pyrimidin-2-amine

Calculated chemistry of [ 66521-66-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.67
TPSA : 64.69 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -7.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.25
Log Po/w (XLOGP3) : 0.45
Log Po/w (WLOGP) : 1.13
Log Po/w (MLOGP) : -0.04
Log Po/w (SILICOS-IT) : 1.25
Consensus Log Po/w : 0.81

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.81
Solubility : 2.68 mg/ml ; 0.0156 mol/l
Class : Very soluble
Log S (Ali) : -1.38
Solubility : 7.23 mg/ml ; 0.042 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.43
Solubility : 0.0635 mg/ml ; 0.000369 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.03

Safety of [ 66521-66-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 66521-66-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 66521-66-2 ]
  • Downstream synthetic route of [ 66521-66-2 ]

[ 66521-66-2 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 506-93-4 ]
  • [ 55314-16-4 ]
  • [ 66521-66-2 ]
YieldReaction ConditionsOperation in experiment
85% With sodium hydroxide In butan-1-ol for 16 h; Reflux 3-(Dimethylamino)-1-(pyridine-3-yl) prop-2-en-1-one (15.4 g, 0.088 mol), guanidine nitrate (10.7 g, 0.088 mol), and sodium hydroxide (3.5 g, 0.088 mol) were dissolved in n-butanol (120 mL).
The mixture was heated to reflux with stirring and maintained for 16 hours.
The reaction mixture was then cooled to room temperature.
The solid was collected and washed with water (400 mL).
The desired product was dried under vacuum for three days and 12.7 g of yellow crystals of desired product was obtained (yield: 85percent); 1H NMR (500 MHz, CDCl3) δ 5.15 (br., 2H), 7.09 (d, 1H), 7.44 (in, 1H), 8.33 (d, 1H), 8.42 (d, 1H), 8.73 (d, 1H), 9.22 (s, 1H). LC-MS (m/z) calculated, 172.2, found 173.2 [M+H]+.
1.18 g With sodium hydroxide In butan-1-ol at 90℃; for 0.333333 h; Microwave irradiation The obtained compound 3 followed by 3-(dimethylamino)-1-(pyridin-3-yl) prop-2-en-1-one (0.1 mol), guanidine nitrate(0.1 mol), sodium hydroxide (0.1 mol), and n-butanol (12.5 mL) was irradiated in the microwave synthesizer at 90 C for 20 min. Aftercompletion of the reaction mixture poured into ice-cold water andthe resulting solid was filtered and washed with water. The obtainedsolid of compound 4 (1.18 g) was dried under vacuum.Melting point 190-192 °C, ES-MS (M1) found (m/z): 173.1.
Reference: [1] Organic Process Research and Development, 2008, vol. 12, # 3, p. 490 - 495
[2] Patent: US9095622, 2015, B2, . Location in patent: Page/Page column 31
[3] Chemical Communications, 2010, vol. 46, # 14, p. 2450 - 2452
[4] Synlett, 2016, vol. 27, # 15, p. 2233 - 2236
[5] European Journal of Medicinal Chemistry, 2017, vol. 128, p. 1 - 12
[6] Journal of Molecular Structure, 2018, vol. 1171, p. 541 - 550
  • 2
  • [ 483324-01-2 ]
  • [ 66521-66-2 ]
YieldReaction ConditionsOperation in experiment
87% With ammonium hydroxide In water at 80℃; for 16 h; Sealed tube Preparation of 4-pyridin-3-yl-pyrimidin-2-ylamine lll-b In a sealed tube, a solution of lll-a (1 .18 g, 6.16 mmol) in 30percent NH4OH (12 mL) was heated at δΟ ' for 16h. After cooling, the precipitate was isolated by filtration, washed with water and dried under vacuum to give the title compound lll-b as a beige solid (925 mg, 87 percent). H NMR (400 MHz, DMSO-d6) δ 9.23 (d, J = 2.1 Hz, 1 H), 8.69 (dd, J = 4.7, 1 .3 Hz, 1 H), 8.43 - 8.38 (m, 1 H), 8.36 (d, J = 5.1 Hz, 1 H), 7.53 (dd, J = 8.0, 4.8 Hz, 1 H), 7.21 (d, J = 5.1 Hz, 1 H), 6.76 (s, 2H).
Reference: [1] Patent: WO2014/202763, 2014, A1, . Location in patent: Page/Page column 48-49
  • 3
  • [ 593-85-1 ]
  • [ 55314-16-4 ]
  • [ 66521-66-2 ]
YieldReaction ConditionsOperation in experiment
66% With sodium hydroxide In butan-1-ol at 120℃; for 2 h; NaOH (0.78 g, 19.5 mmol) was added to a mixture of 3-(dimethylamino)-l-(pyridin-3- yl)prop-2-en-l-one (3.52 g, 20.0 mmol) and guanidine carbonate (1.80 g) in n-butanol (20 mL). The mixture was heated at 1200C for 2 h. After cooling, the precipitates formed was collected by filtration and dried under vacuum to afford the desired product (2.3g, 66percent). LCMS: (M+H)+= 173.2.
Reference: [1] Patent: WO2010/96395, 2010, A1, . Location in patent: Page/Page column 36
[2] Patent: WO2008/130944, 2008, A1, . Location in patent: Page/Page column 15-16
  • 4
  • [ 50-01-1 ]
  • [ 55314-16-4 ]
  • [ 66521-66-2 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 66, p. 61458 - 61467
[2] MedChemComm, 2015, vol. 6, # 10, p. 1816 - 1825
[3] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 11, p. 3860 - 3874
[4] Organic and Biomolecular Chemistry, 2009, vol. 7, # 24, p. 5129 - 5136
[5] Chemical Communications, 2010, vol. 46, # 7, p. 1118 - 1120
[6] Journal of the American Chemical Society, 2012, vol. 134, # 1, p. 700 - 706
[7] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 5, p. 1296 - 1301
[8] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3714 - 3718
[9] Journal of Organic Chemistry, 2016, vol. 81, # 23, p. 11788 - 11801
[10] Archiv der Pharmazie, 2017, vol. 350, # 3-4,
  • 5
  • [ 3993-78-0 ]
  • [ 1692-25-7 ]
  • [ 66521-66-2 ]
YieldReaction ConditionsOperation in experiment
72% With 1-(2,6-diisopropylphenyl)-3-(2-oxo-2-(2,4,6-tri-tert-butylphenylamino)ethyl)-1H-imidazol-3-ium bromide; palladium diacetate; sodium hydroxide In water; dimethyl sulfoxide at 100℃; for 10 h;          Pd(OAc)(35.00 mg, 0.15 mmol) and 1-(2,6-diisopropylphenyl)-3-(2-oxo-2-(2,4,6-tri-tert-butylphenylamino)ethyl)-1H-imidazol-3-iumbromide (96.00 mg, 0.15 mmol) was dissolved in 10 ml of DMSO : H2O,and 4-chloropyrimidin-2-amine (2.00 g, 15.43 mmol), NaOH (0.93 g, 23.15 mmol),pyridin-3-ylboronic acid (2.28 g, 18.5 mmol)  were added. The mixture was heated to 100 oCand stirred for 10h. After cooling, the mixturewas poured into EtOAc (40.0 mL and washed with water (2 ×10.0 mL), brine (2 × 25.0 mL), then dried over MgSO4, evaporation ofthe solvent under reduced pressure provided the crude product, which waspurified by column chromatography (hexane : EtOAc = 1:1) afford product as off white solid 1.92 g, 11.15 mmol) in 72percent yield. 1HNMR (300 MHz, DMSO): δ 9.23(dd, J =1.5 Hz, 1H), 8.68 (dd, J1= 3.0 Hz, J2 = 1.8 Hz,1H), 8.41-8.35 (m, 2H), 7.55-7.50 (m, 1H), 7.20 (d, J1 = 5.1 Hz, 1H), 6.78 (bs, 2H);   13C NMR (75 MHz, CDCl3): δ 163.8, 161.6, 159.4, 151.1, 148.0, 134.1,123.7, 106.0. HRMS(ESI) calcd. for C9H9N4 [M+H]+173.0827, found 173.0825.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 49, p. 6657 - 6661
  • 6
  • [ 506-93-4 ]
  • [ 55314-16-4 ]
  • [ 66521-66-2 ]
YieldReaction ConditionsOperation in experiment
93% for 12 h; Reflux General procedure: A mixture of compound 5 (1 mmol), guanidine nitrate (2 mmol), anhydrous K2CO3 (5 mmol) in n-butanol (10 ml) was refluxed for 12 h. After cooling, the solution was poured into H2O (30 ml) and then extracted with ethyl acetate (3x20 ml). The combined organic layer was concentrated in vacuo and then purified by recrystallisation with diethyl ether.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 3024 - 3028
[2] Angewandte Chemie, International Edition, 2015, vol. 54, # 1, p. 179 - 183[3] Angewandte Chemie, 2015, vol. 127, # 1, p. 181 - 185,5
[4] Organic and Biomolecular Chemistry, 2013, vol. 11, # 11, p. 1822 - 1839
  • 7
  • [ 350-03-8 ]
  • [ 66521-66-2 ]
Reference: [1] ChemMedChem, 2011, vol. 6, # 11, p. 2009 - 2018
[2] Organic and Biomolecular Chemistry, 2013, vol. 11, # 11, p. 1822 - 1839
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 33, p. 8551 - 8556[4] Angew. Chem., 2013, vol. 125, # 33, p. 8713 - 8718,6
[5] Organic Process Research and Development, 2008, vol. 12, # 3, p. 490 - 495
[6] Angewandte Chemie, International Edition, 2015, vol. 54, # 1, p. 179 - 183[7] Angewandte Chemie, 2015, vol. 127, # 1, p. 181 - 185,5
[8] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 5, p. 1296 - 1301
[9] Patent: US9095622, 2015, B2,
[10] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 3024 - 3028
[11] RSC Advances, 2016, vol. 6, # 66, p. 61458 - 61467
[12] RSC Advances, 2016, vol. 6, # 66, p. 61458 - 61467
[13] Synlett, 2016, vol. 27, # 15, p. 2233 - 2236
[14] Journal of Organic Chemistry, 2016, vol. 81, # 23, p. 11788 - 11801
[15] European Journal of Medicinal Chemistry, 2017, vol. 128, p. 1 - 12
[16] Archiv der Pharmazie, 2017, vol. 350, # 3-4,
[17] Journal of Molecular Structure, 2018, vol. 1171, p. 541 - 550
[18] European Journal of Organic Chemistry, 2017, vol. 2017, # 29, p. 4247 - 4254
  • 8
  • [ 55314-16-4 ]
  • [ 66521-66-2 ]
Reference: [1] Russian Journal of Organic Chemistry, 2011, vol. 47, # 8, p. 1222 - 1226
[2] Angewandte Chemie - International Edition, 2013, vol. 52, # 33, p. 8551 - 8556[3] Angew. Chem., 2013, vol. 125, # 33, p. 8713 - 8718,6
[4] Synthesis, 2007, # 14, p. 2121 - 2124
[5] Russian Journal of Organic Chemistry, 2011, vol. 47, # 8, p. 1222 - 1226
[6] Russian Journal of Organic Chemistry, 2011, vol. 47, # 8, p. 1222 - 1226
  • 9
  • [ 1392279-39-8 ]
  • [ 50-01-1 ]
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Reference: [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 29, p. 4247 - 4254
  • 10
  • [ 1144477-16-6 ]
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Reference: [1] Russian Journal of Organic Chemistry, 2011, vol. 47, # 8, p. 1222 - 1226
  • 11
  • [ 420-04-2 ]
  • [ 55314-16-4 ]
  • [ 88-74-4 ]
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Reference: [1] Russian Journal of Organic Chemistry, 2011, vol. 47, # 8, p. 1222 - 1226
  • 12
  • [ 55314-16-4 ]
  • [ 66521-66-2 ]
Reference: [1] ChemMedChem, 2011, vol. 6, # 11, p. 2009 - 2018
  • 13
  • [ 50-01-1 ]
  • [ 55314-16-4 ]
  • [ 66521-66-2 ]
Reference: [1] Molecules, 2008, vol. 13, # 4, p. 818 - 830
  • 14
  • [ 626-55-1 ]
  • [ 66521-66-2 ]
Reference: [1] Patent: WO2014/202763, 2014, A1,
  • 15
  • [ 66521-66-2 ]
  • [ 404844-11-7 ]
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 49, p. 6657 - 6661
[2] Organic Process Research and Development, 2008, vol. 12, # 3, p. 490 - 495
[3] Angewandte Chemie, International Edition, 2015, vol. 54, # 1, p. 179 - 183[4] Angewandte Chemie, 2015, vol. 127, # 1, p. 181 - 185,5
[5] Patent: US9095622, 2015, B2,
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